DE69712100T2 - Valproinsäure enthaltende mikrosphären für orale verabreichung - Google Patents
Valproinsäure enthaltende mikrosphären für orale verabreichungInfo
- Publication number
- DE69712100T2 DE69712100T2 DE69712100T DE69712100T DE69712100T2 DE 69712100 T2 DE69712100 T2 DE 69712100T2 DE 69712100 T DE69712100 T DE 69712100T DE 69712100 T DE69712100 T DE 69712100T DE 69712100 T2 DE69712100 T2 DE 69712100T2
- Authority
- DE
- Germany
- Prior art keywords
- pharmaceutical
- microspheres according
- active ingredient
- valproic acid
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 title claims description 101
- 239000004005 microsphere Substances 0.000 title claims description 89
- 229960000604 valproic acid Drugs 0.000 title claims description 58
- 239000000203 mixture Substances 0.000 claims description 63
- 239000004480 active ingredient Substances 0.000 claims description 57
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 claims description 56
- 239000012876 carrier material Substances 0.000 claims description 37
- 239000011159 matrix material Substances 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- -1 alkali metal salt Chemical class 0.000 claims description 20
- 235000013871 bee wax Nutrition 0.000 claims description 18
- 239000012166 beeswax Substances 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 10
- 239000001993 wax Substances 0.000 claims description 10
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 9
- 125000005456 glyceride group Chemical group 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- 239000012188 paraffin wax Substances 0.000 claims description 8
- FETSQPAGYOVAQU-UHFFFAOYSA-N glyceryl palmitostearate Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O FETSQPAGYOVAQU-UHFFFAOYSA-N 0.000 claims description 7
- 239000003921 oil Substances 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 239000004359 castor oil Substances 0.000 claims description 6
- 235000019438 castor oil Nutrition 0.000 claims description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- DMBUODUULYCPAK-UHFFFAOYSA-N 1,3-bis(docosanoyloxy)propan-2-yl docosanoate Chemical group CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCCCCCC DMBUODUULYCPAK-UHFFFAOYSA-N 0.000 claims description 5
- 150000002314 glycerols Chemical class 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- 150000005690 diesters Chemical class 0.000 claims description 4
- 229940075507 glyceryl monostearate Drugs 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 claims description 4
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 claims description 3
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 claims description 3
- 229940046813 glyceryl palmitostearate Drugs 0.000 claims description 3
- 159000000003 magnesium salts Chemical class 0.000 claims description 3
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 235000003599 food sweetener Nutrition 0.000 claims description 2
- 230000005484 gravity Effects 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 2
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 2
- 239000003765 sweetening agent Substances 0.000 claims description 2
- 150000005691 triesters Chemical class 0.000 claims description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims 1
- 239000011256 inorganic filler Substances 0.000 claims 1
- 229910003475 inorganic filler Inorganic materials 0.000 claims 1
- AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 42
- 229940084026 sodium valproate Drugs 0.000 description 42
- 241001440269 Cutina Species 0.000 description 21
- 238000009472 formulation Methods 0.000 description 16
- 238000004090 dissolution Methods 0.000 description 14
- 239000003826 tablet Substances 0.000 description 13
- 230000003111 delayed effect Effects 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 239000013543 active substance Substances 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 238000013268 sustained release Methods 0.000 description 6
- 239000012730 sustained-release form Substances 0.000 description 6
- OIQOAYVCKAHSEJ-UHFFFAOYSA-N 2-[2,3-bis(2-hydroxyethoxy)propoxy]ethanol;hexadecanoic acid;octadecanoic acid Chemical compound OCCOCC(OCCO)COCCO.CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O OIQOAYVCKAHSEJ-UHFFFAOYSA-N 0.000 description 5
- 238000007922 dissolution test Methods 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 235000013618 yogurt Nutrition 0.000 description 5
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000007939 sustained release tablet Substances 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- 229940102566 valproate Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000007765 cera alba Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 235000019640 taste Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229960000278 theophylline Drugs 0.000 description 2
- 108010011485 Aspartame Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 229940075529 glyceryl stearate Drugs 0.000 description 1
- 238000001033 granulometry Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
- 229960000991 ketoprofen Drugs 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Neurosurgery (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9612201A FR2754177B1 (fr) | 1996-10-07 | 1996-10-07 | Microspheres pharmaceutiques d'acide valproique pour administration orale |
| PCT/FR1997/001762 WO1998015268A1 (fr) | 1996-10-07 | 1997-10-03 | Microspheres pharmaceutiques d'acide valproique pour administration orale |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69712100D1 DE69712100D1 (de) | 2002-05-23 |
| DE69712100T2 true DE69712100T2 (de) | 2002-11-28 |
Family
ID=9496427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69712100T Expired - Lifetime DE69712100T2 (de) | 1996-10-07 | 1997-10-03 | Valproinsäure enthaltende mikrosphären für orale verabreichung |
Country Status (40)
| Country | Link |
|---|---|
| US (3) | US20020001598A1 (et) |
| EP (1) | EP0956010B1 (et) |
| JP (1) | JP3523270B2 (et) |
| KR (1) | KR100334687B1 (et) |
| CN (1) | CN100367945C (et) |
| AR (1) | AR013613A1 (et) |
| AT (1) | ATE216228T1 (et) |
| AU (1) | AU731235B2 (et) |
| BR (1) | BR9712268A (et) |
| CA (1) | CA2267096C (et) |
| CO (1) | CO4900080A1 (et) |
| CZ (1) | CZ288876B6 (et) |
| DE (1) | DE69712100T2 (et) |
| DK (1) | DK0956010T3 (et) |
| DZ (1) | DZ2316A1 (et) |
| EE (1) | EE03744B1 (et) |
| EG (1) | EG24070A (et) |
| ES (1) | ES2174293T3 (et) |
| FR (1) | FR2754177B1 (et) |
| HK (1) | HK1021939A1 (et) |
| HR (1) | HRP970537B1 (et) |
| HU (1) | HU225103B1 (et) |
| ID (1) | ID24596A (et) |
| IL (1) | IL128745A (et) |
| IS (1) | IS1985B (et) |
| ME (1) | ME00664B (et) |
| MY (1) | MY120521A (et) |
| NO (1) | NO325723B1 (et) |
| NZ (1) | NZ334399A (et) |
| PL (1) | PL190105B1 (et) |
| PT (1) | PT956010E (et) |
| RS (1) | RS49602B (et) |
| RU (1) | RU2177315C2 (et) |
| SI (1) | SI0956010T1 (et) |
| SK (1) | SK282113B6 (et) |
| TR (1) | TR199900789T2 (et) |
| TW (1) | TW508251B (et) |
| UY (1) | UY24738A1 (et) |
| WO (1) | WO1998015268A1 (et) |
| ZA (1) | ZA978954B (et) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1187601E (pt) | 1999-06-07 | 2005-11-30 | Altana Pharma Ag | Nova forma de preparacao e a administracao compreendendo um inibidor da bomba de protoes instavel em meio acido |
| CA2508855A1 (en) * | 2002-12-16 | 2004-07-01 | Frank Slade Abbott | Valproic acid analogues and pharmaceutical compositions thereof |
| TWI547431B (zh) * | 2004-06-09 | 2016-09-01 | 史密斯克萊美占公司 | 生產藥物之裝置及方法 |
| US20060069040A1 (en) * | 2004-09-07 | 2006-03-30 | Mortimer Mamelak | GHB compositions |
| US9149433B2 (en) * | 2004-11-30 | 2015-10-06 | Basf Corporation | Method for formation of micro-prilled polymers |
| US20060252830A1 (en) * | 2005-05-06 | 2006-11-09 | Brandon Stephen F | Method for the treatment of magnesium and potassium deficiencies |
| US20060252831A1 (en) * | 2005-05-06 | 2006-11-09 | Christopher Offen | Method for the treatment of magnesium and potassium deficiencies |
| US8992422B2 (en) | 2006-03-23 | 2015-03-31 | Ethicon Endo-Surgery, Inc. | Robotically-controlled endoscopic accessory channel |
| CN101543631B (zh) * | 2008-03-28 | 2012-01-11 | 沈阳兴齐制药有限公司 | 含蜂蜡的微球基质、含有它的药物组合物及其用途 |
| JP5866279B2 (ja) * | 2009-05-12 | 2016-02-17 | 株式会社アモーレパシフィックＡｍｏｒｅｐａｃｉｆｉｃ Ｃｏｒｐｏｒａｔｉｏｎ | 脱毛防止又は育毛促進のための組成物 |
| CN105899197A (zh) * | 2013-11-13 | 2016-08-24 | 蒂洛特斯制药股份有限公司 | 多颗粒药物递送系统 |
| CN104013596A (zh) * | 2014-05-16 | 2014-09-03 | 安士制药（中山）有限公司 | 一种丙戊酸软胶囊及其制备方法 |
| CN105456217A (zh) * | 2014-08-27 | 2016-04-06 | 捷思英达医药技术（上海）有限公司 | 一种双丙戊酸钠缓释剂组合物及其制备方法 |
| CN110998957B (zh) | 2017-08-24 | 2023-03-24 | 三井化学株式会社 | 电池用非水电解液及锂二次电池 |
| KR20200035095A (ko) | 2017-08-24 | 2020-04-01 | 미쓰이 가가쿠 가부시키가이샤 | 리튬 이차 전지 및 비수 전해액 |
| CN111012753A (zh) * | 2020-01-07 | 2020-04-17 | 仁和堂药业有限公司 | 一种提高丙戊酸钠片剂稳定性的方法 |
| CN112274499A (zh) * | 2020-11-16 | 2021-01-29 | 仁和堂药业有限公司 | 一种提高丙戊酸钠片剂稳定性的方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2293974A1 (fr) * | 1973-03-02 | 1976-07-09 | Kaltenbach Roger | Procede et dispositif pour la granulation reguliere de divers produits |
| US5212326A (en) * | 1979-08-20 | 1993-05-18 | Abbott Laboratories | Sodium hydrogen divalproate oligomer |
| DK150008C (da) * | 1981-11-20 | 1987-05-25 | Benzon As Alfred | Fremgangsmaade til fremstilling af et farmaceutisk oralt polydepotpraeparat |
| IL72381A (en) * | 1983-07-20 | 1988-03-31 | Sanofi Sa | Pharmaceutical composition based on valproic acid |
| US5185159A (en) * | 1983-07-20 | 1993-02-09 | Sanofi | Pharmaceutical composition based on valproic acid and a process for preparing it |
| US4913906B1 (en) * | 1985-02-28 | 2000-06-06 | Yissum Res Dev Co | Controlled release dosage form of valproic acid |
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1996
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1997
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